Synthesis, Characterization, and Antimicrobial Activity of a Novel Trisazo Dye from 3-Amino-4H-thieno[3,4-c][1]benzopyran-4-one

Abstract

A new trisazo dye has been synthesized by coupling the diazonium ion of 3-amino-4H thieno[3,4-c][1]benzopyran-4-one with 2-tert-butyl-4-methoxyphenol. The newly prepared trisazo dye was characterized by its physical, elemental, and spectroscopic data. 2D-NMR (COSY, HSQC, and HMBC) techniques were used to secure the structural assignments. The new trisazo dye (compound 7) along with precursors 3, 4, and 6 was screened by microdilution susceptibility assay for antibacterial and antifungal activities towards eight bacterial strains and three yeasts selected on the basis of their relevance as human pathogens. The results showed that compound 7 (MIC = 2–128 μg/mL) was the most active as compared with its precursors. The most resistant microorganisms were V. cholerae NB2 and V. cholerae SG24, whereas the most sensitive microorganism was C. neoformans. The overall results of this study indicated that compound 7 had the greatest potential value against both yeasts and multidrug-resistant bacteria, so further investigation is warranted.

Synthesis, characterization, antimicrobial activities and electrochemical behavior of new phenolic azo dyes from two thienocoumarin amines

“…The other compounds exhibited microbicidal effect on all the sensitive microorganisms. The results of the present investigation are in agreement with those reported in the literature describing the antimicrobial activities of some azo compounds and phenol derivatives against a wide range of microorganisms among which S. aureus, [31][32][33][34][35] P. aeruginosa, [31][32][33]36 V. cholera, [37][38][39][40] B. subtilis, [37][38][39][40] C. albicans, 31,33,36,40 C. neoformans 36,[42][43][44] and C. tropicalis. [45][46][47][48] .…”

Antimicrobial Activity of Novel Functionally Substituted Monocyclic and Spirocyclic Cyclohexane Derivatives

“…Currently there is emergence of pan drug resistant bacteria showing resistance to almost all the available antibiotics in the market (Bielawski et al, 2017). Drug development studies focus on functionally substituted chemical compounds with potential antimicrobial properties and their unique mode of action to overcome antimicrobial resistance (Tsemeugne et al, 2018).…”

Synthesis, Characterization and Biological Evaluation of some Novel Substituted Indole-Coumarin Derivatives as Potential Antibacterial and Antifungal Agents

“…The development of multidrug-resistant bacteria and the effects of global warming are two of the most significant problems that contemporary scientists have faced in recent decades. The fact that many pathogenic microorganisms responsible for a variety of human and animal diseases have developed mechanisms of resistance to conventional therapies has prompted extensive research in the fields of natural and synthetic chemistry with the goal of discovering new drug classes with significantly improved therapeutic profiles than those currently available [1]. In this regard, the antimicrobial activities of numerous classes of organic substances, including phenols [2,3], coumarins [4][5][6][7][8], thiophenes [9], quinones [10], and azo compounds [11], are currently the focus of drug discovery efforts around the world.…”

“…Molecular and/or biologic conjugates of this kind, it is anticipated, will become the main form of targeted infectious disease therapy in the long run, according to the researchers. Combining two or more potentially bioactive substructures to form an integrated new molecular framework with increased anticipated therapeutic firepower is a conceptually simple concept that has proven to be extremely successful in the context of infectious diseases that necessitate effective killing of microbes [1].…”